Corey-Nicolaou Macrolactonization

• General Characteristics

The macrolactonization reaction using 2,2’-dipyridyldisulfide and triphenylphosphine is known as the Corey-Nicolaou reaction. The cyclization step usually requires a high temperature. The addition of silver salts (e.g. AgBF₄) for the activation of the pyridylthioester was later found to accelerate the reaction dramatically.

• General References

・Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. DOI: 10.1021/ja00824a073
・Corey, E. J.; Nicolaou, K .C.; Melvin, L. S., Jr. J. Am. Chem. Soc. 1975, 97, 653. DOI: 10.1021/ja00836a036
・Modification: Gerlach, H.; Thalmann, A. Helv. Chim. Acta 1974, 57, 2661.

• Reaction Mechanism

• Examples

 The synthesis of zearalenone.^[1]

• Experimental Procedure

• Experimental Tips

• References

[1] Corey, E. J.; Nicolaou, K. C. J. Am. Chem. Soc. 1974, 96, 5614. DOI: 10.1021/ja00824a073

• Related Books

 

 

 

dipyridildisulfide, macrolactonization